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Archive | September 2011

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Gone to Hell

I’m taking my handbasket up to the Hell, Michigan area this weekend, but I’m leaving the internet behind.  Catch you all in a couple of days. About these ads

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Question 118: How do I break up with someone?

Hi, Captain Awkward, My current boyfriend and I have been seeing each other since January of this year. To cut to the chase, I don’t know how to break up with him. When we first started dating he was exactly what I was looking for, but as time has gone on I now see him […]

Short films in Chicago this Thursday

There are still a few seats left for the New Visions Film Festival this Thursday night in the South Loop.  My film has a makeover montage that is a critique of makeover montages AND many awkward moments!  Only $10 ($5 for students with ID).    

Question #117: How is this relationship like ill-fitting pants?

Dear Captain Awkward: Maybe you can help me untangle my brain? I’ve been dating a guy for eight months. We live about an hour apart, and made up for irregular facetime with hours-long phone calls. Then bad things happened in each of our lives, and the rainbows and unicorns we’d started with disappeared. The last […]

Question #116: How do I seduce women? (Yes, this was an actual question).

Dear Captain Awkward I’m a young guy, 20s. I was a bit of late bloomer, and have only limited (but a little!) experience seducing women. I feel like I might’ve missed some cues because of a very inactive teenage sex life. So my question is about the very cliched topic of wooing and fucking the […]

How to locate low-cost mental health care in the US and Canada (Guest Post!)

Long-time reader The Mental Health Mountie has compiled some recommendations for affordable mental health care for us.  Hopefully you will find it useful.  If you’ve tried any of these methods and can tell us how it went or if you can suggest additional resources, let us know in the comments. ———————————– Therapy on Sale You’ve spoken to […]

The Self-Centered Friend: Return of the Side-Eye (Question #115)

Dear Captain Awkward, I’ve been reading your column for a while, and am dearly in need of advice. To cut right to the chase, I have a friend. He is a lovely lovely person, but there are some things about him that have been making maintaining that friendship well…difficult. Complicating this is the fact that […]

Reader question #114: How do I reconnect with my estranged brother and help him form a relationship with his niece?

Dear Captain Awkward -  I write for a reality check from you and your wise readers regarding the plan I have devised going forward with my brother. The backstory: my brother’s wife has chronic health problems, and some mental health issues as well (who wouldn’t?). She is totally isolated from her family, and basically only […]

Question #113: How do I make plans with flaky San Francisco people?

Dear Captain Awkward: So I am a recentish transplant to San Francisco at 28. I have many acquaintances here from various parts of my life, as SF is one of those cities people just end up in. These people are not connected to each other in any way. As I attempt to build a friendship […]

Reader question #112: My mom wants to call herself my partners’ kid’s grandma.

Dear Captain, I’ve been part of a polyamorous triad (3-person relationship were everyone is in a relationship with each other) for a little over year now. It’s a serious and committed relationship. We’re in it for the long haul. My two partners have a kid together (herein Kiddo). Kiddo will be two this weekend. I […]


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